AR064432A1 - PROCESS FOR THE PREPARATION OF COMPOUNDS 6, 6-DIMETHYL-3-AZA-BIKE - Google Patents
PROCESS FOR THE PREPARATION OF COMPOUNDS 6, 6-DIMETHYL-3-AZA-BIKEInfo
- Publication number
- AR064432A1 AR064432A1 ARP070105709A ARP070105709A AR064432A1 AR 064432 A1 AR064432 A1 AR 064432A1 AR P070105709 A ARP070105709 A AR P070105709A AR P070105709 A ARP070105709 A AR P070105709A AR 064432 A1 AR064432 A1 AR 064432A1
- Authority
- AR
- Argentina
- Prior art keywords
- dimethyl
- mixture
- compounds
- formulas
- formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un proceso para preparar 6,6-dimetil-3-aza-biciclo[3.1.0]hexan-2-sulfonato, un intermediario util en la preparacion eficiente de (1R,2S,5S)-6,6-dimetil-3-azabiciclo[3.1.0]hexan-2-carboxilato de metilo y sus ésteres y sales, procesos para preparar (1R,2S,5S)-6,6-dimetil-3-azabiciclo[3.1.0]hexan-2-carboxilato de metilo y ésteres y sales del mismo a partir del sulfonato intermediario y procesos para preparar 6,6- dimetil-3-aza-biciclo[3.1.0]hexan-2-sulfonato. Reivindicacion 1: Un proceso para preparar una mezcla de los compuestos aductos 6,6-dimetil-3-azabiciclo[3.1.0]hexan-2-sulfonato de sodio de formulas (1) y (2), el proceso que comprende hacer reaccionar una solucion orgánica de una mezcla de compuestos iminas de formulas (3) y (4) con una fuente de bisulfito sodico. Reivindicacion 8: Un proceso para la provision de una mezcla de compuestos nitrilo de formulas (5) y (6), el proceso que comprende: (i) hacer reaccionar anhídrido caronico con bencilamina para formar la 2,4- diona de formula (7), (ii) reducir la diona de formula (7) al compuesto 3-aza-bencil-biciclohexano de formula (8); (iii) reducir el compuesto de formula (8) a 6,6-dimetil-3-aza- biciclo[3.1.0]hexano; (iv) oxidar el producto derivado de hexano proveniente de la reduccion del paso (iii) para suministrar una mezcla que comprende las iminas de formulas (3) y (4); (v) hacer reaccionar la mezcla de los compuestos producida en el paso (iv) de oxidacion con bisulfito sodico para suministrar los compuestos aductos transbisulfíticos de formulas (1) y (2); (vi) hacer reaccionar la mezcla de compuestos aductos bisulfíticos producida en el paso (v) con una fuente de cianato-aducto para formar la correspondiente mezcla de compuestos nitrilo de formulas (5) y (6). Reivindicacion 16: El compuesto de formula (1). Reivindicacion 17: El compuesto de formula (2).A process for preparing 6,6-dimethyl-3-aza-bicyclo [3.1.0] hexane-2-sulfonate, an intermediate useful in the efficient preparation of (1R, 2S, 5S) -6,6-dimethyl-3- azabicyclo [3.1.0] methyl hexan-2-carboxylate and its esters and salts, processes for preparing (1R, 2S, 5S) -6,6-dimethyl-3-azabicyclo [3.1.0] hexan-2-carboxylate methyl and esters and salts thereof from the intermediate sulfonate and processes for preparing 6,6-dimethyl-3-aza-bicyclo [3.1.0] hexane-2-sulfonate. Claim 1: A process for preparing a mixture of the 6,6-dimethyl-3-azabicyclo [3.1.0] hexane-2-sulphonate adducts compounds of formulas (1) and (2), the process comprising reacting an organic solution of a mixture of imine compounds of formulas (3) and (4) with a source of sodium bisulfite. Claim 8: A process for the provision of a mixture of nitrile compounds of formulas (5) and (6), the process comprising: (i) reacting caronic anhydride with benzylamine to form the 2,4-dione of formula (7 ), (ii) reduce the dione of formula (7) to the compound 3-aza-benzyl-bicyclohexane of formula (8); (iii) reduce the compound of formula (8) to 6,6-dimethyl-3-azabicyclo [3.1.0] hexane; (iv) oxidize the hexane-derived product from the reduction of step (iii) to provide a mixture comprising the imines of formulas (3) and (4); (v) reacting the mixture of the compounds produced in the oxidation step (iv) with sodium bisulfite to deliver the transbisulfitic adduct compounds of formulas (1) and (2); (vi) reacting the mixture of bisulfitic adduct compounds produced in step (v) with a cyanate-adduct source to form the corresponding mixture of nitrile compounds of formulas (5) and (6). Claim 16: The compound of formula (1). Claim 17: The compound of formula (2).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87629606P | 2006-12-20 | 2006-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR064432A1 true AR064432A1 (en) | 2009-04-01 |
Family
ID=39589116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP070105709A AR064432A1 (en) | 2006-12-20 | 2007-12-18 | PROCESS FOR THE PREPARATION OF COMPOUNDS 6, 6-DIMETHYL-3-AZA-BIKE |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8158807B2 (en) |
| EP (1) | EP2129658A2 (en) |
| JP (1) | JP5431956B2 (en) |
| CN (1) | CN101611001B (en) |
| AR (1) | AR064432A1 (en) |
| CA (1) | CA2672701A1 (en) |
| MX (1) | MX2009006865A (en) |
| WO (1) | WO2008082508A2 (en) |
| ZA (1) | ZA200904333B (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010005809A (en) * | 2007-11-28 | 2010-06-09 | Schering Corp | Dehydrohalogenation process for the preparation of intermediates useful in providing 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds. |
| CN102816106A (en) | 2008-06-24 | 2012-12-12 | 默沙东公司 | Biocatalytic processes for the preparation of substantially stereomerically pure fused bicyclic proline compounds |
| WO2012049688A1 (en) | 2010-10-12 | 2012-04-19 | Arch Pharmalabs Limited | An improved process for the preparation of racemic 6, 6- dimethyl-3-azabicyclo-[3.1.0]-hexane and its salts, a key raw material for hcv inhibitor. |
| CN103748059A (en) * | 2011-05-13 | 2014-04-23 | 弗特克斯药品有限公司 | Process for the preparation of protease inhibitors |
| WO2012158513A1 (en) * | 2011-05-13 | 2012-11-22 | Vertex Pharmaceuticals Incorporated | Processes and intermediates |
| JP2013010732A (en) | 2011-06-03 | 2013-01-17 | Sumitomo Chemical Co Ltd | Method for producing proline compound |
| CN103435532B (en) * | 2013-09-02 | 2015-07-08 | 苏州永健生物医药有限公司 | Synthetic method of boceprevir intermediate |
| CN103664739B (en) * | 2013-12-10 | 2016-04-27 | 湖南科源生物制品有限公司 | A kind of preparation method of Telaprevir intermediate |
| CN103910669B (en) * | 2014-04-04 | 2015-10-21 | 苏州景泓生物技术有限公司 | The preparation method of BMS-477118 key intermediate |
| CN113999160B (en) * | 2021-10-21 | 2022-12-27 | 江苏省药物研究所有限公司 | Preparation method of 6,6-dimethyl-3-azabicyclo [3.1.0] hexane |
| CN114163375B (en) * | 2021-12-10 | 2023-09-05 | 浙江新和成股份有限公司 | Synthesis method of 6,6-dimethyl-3-azabicyclo [3.1.0] hexane or derivative thereof |
| CN114544801B (en) * | 2022-01-20 | 2023-02-28 | 汉瑞药业(荆门)有限公司 | GC-FID detection method of azabicyclo [3.1.0] hexane |
| CN114591217B (en) * | 2022-03-18 | 2024-04-16 | 浙江新和成股份有限公司 | Preparation method of 6, 6-dimethyl-3-azabicyclo- [3.1.0] -hexane and lactone intermediate thereof |
| CN114751853B (en) * | 2022-04-11 | 2023-10-13 | 扬州联澳生物医药有限公司 | Process for preparing 6, 6-dimethyl-3-azabicyclo [3.1.0] hexane compounds |
| CN114957087A (en) * | 2022-04-13 | 2022-08-30 | 湖南复瑞生物医药技术有限责任公司 | Preparation method of intermediate of palovaried |
| CN114605311B (en) * | 2022-05-16 | 2022-07-15 | 南京桦冠生物技术有限公司 | Process for the preparation of intermediates of the drug nitratrelvir useful in the treatment of novel coronaviruses |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183857A (en) * | 1978-07-06 | 1980-01-15 | Shell Oil Company | 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione |
| CA1117125A (en) * | 1978-03-01 | 1982-01-26 | Ronald F. Mason | 2-cyano-3-azabicyclo¬3.1.0|hexane compounds |
| US4225499A (en) * | 1978-07-06 | 1980-09-30 | Shell Oil Company | Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile |
| DE2962910D1 (en) * | 1978-10-27 | 1982-07-08 | Shell Int Research | A process for the preparation of 3-azabicyclo(3.1.0)hexane derivatives and modifications thereof |
| AR044694A1 (en) | 2003-06-17 | 2005-09-21 | Schering Corp | PROCESS AND INTERMEDIATE COMPOUNDS FOR THE PREPARATION OF (1R, 2S, 5S) - 3 AZABICICLO [3,1,0] HEXANO-2- CARBOXAMIDE, N- [3- AMINO-1- (CYCLLOBUTILMETILE) - 2, 3 - DIOXOPROPIL] -3- [(2S) - 2 - [[[1,1- DIMETHYTILE] AMINO] CARBONYLAMINE] -3,3-DIMETHYL -1- OXOBUTIL] -6.6 DIMETHYL |
| US7723531B2 (en) * | 2005-12-22 | 2010-05-25 | Schering Corporation | Process for the preparation of 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds and enantiomeric salts thereof |
-
2007
- 2007-12-18 CA CA002672701A patent/CA2672701A1/en not_active Abandoned
- 2007-12-18 MX MX2009006865A patent/MX2009006865A/en active IP Right Grant
- 2007-12-18 US US12/519,488 patent/US8158807B2/en not_active Expired - Fee Related
- 2007-12-18 WO PCT/US2007/025809 patent/WO2008082508A2/en active Application Filing
- 2007-12-18 AR ARP070105709A patent/AR064432A1/en unknown
- 2007-12-18 EP EP07863042A patent/EP2129658A2/en not_active Withdrawn
- 2007-12-18 CN CN200780051474.7A patent/CN101611001B/en not_active Expired - Fee Related
- 2007-12-18 JP JP2009542868A patent/JP5431956B2/en not_active Expired - Fee Related
-
2009
- 2009-06-19 ZA ZA200904333A patent/ZA200904333B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008082508A3 (en) | 2008-09-18 |
| CA2672701A1 (en) | 2008-07-10 |
| WO2008082508A2 (en) | 2008-07-10 |
| JP5431956B2 (en) | 2014-03-05 |
| EP2129658A2 (en) | 2009-12-09 |
| US20100145069A1 (en) | 2010-06-10 |
| CN101611001A (en) | 2009-12-23 |
| CN101611001B (en) | 2015-11-25 |
| US8158807B2 (en) | 2012-04-17 |
| JP2010513501A (en) | 2010-04-30 |
| ZA200904333B (en) | 2010-04-28 |
| MX2009006865A (en) | 2009-08-20 |
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